The control of chemical reactivity at the single-molecule scale offers a unique opportunity for the design and fabrication of advanced nanodevices.1-3 As a prototypical reaction, tautomerization has been extensively explored as a promising tool for manipulating the single-molecule conductance of tetrapyrrole macrocycles absorbed on a surface.4-8 However, the resulting molecular devices were determined to undergo dynamic, spontaneous interconversions even under cryogenic conditions, so that control of tautomeric switching between well-defined and specific states remains challenging. Here, we report the design of a reversible single-molecule switch based on an enol-keto tautomerization reaction, which demonstrates controllable bistability and inhibits spontaneous interconversion even at room temperature. Such control is achieved by modulating the potential energy surface (PES) through a bias-triggered charge injection process. Our results reveal that the device operates through switching between two distinct redox-related PESs with opposite thermodynamic driving forces, i.e., one exhibits strong preference for the conducting enol form, while the other exhibits a preference for the insulating keto form. The described switching mechanism constitutes a promising approach to achieve robust switching devices at the single-molecule scale.